Jackie Shames, friend and co-host of Fill Your Cup is back to chat all things confidence, learning from past relationships, and staying true to who you are. Jackie shares her experiences dating between Miami and New York, how the seasons have been impacting her dating life, and the challenges of balancing personal and professional life. We discuss the the New York influencer scene, friendship dynamics, and podcasting, and we live-text someone Jackie went on a date with.00:00 - 09:30 Navigating Confidence and Dating09:30 - 26:24 Unexpected Encounters26:24 - 28:54 Reflecting on Closure and Moving On28:54 - 29:49 The Importance of Detachment29:49 - 31:25 Running Into an Ex-Fling31:25 - 33:24 Finding Security in a New Relationship33:24 - 36:26 Navigating Dating Patterns and Self-Sabotage36:26 - 43:38 Balancing Personalities in Relationships43:38 - 55:53 Influencer Culture and Personal GrowthSay goodbye to your anxiety and say hello to relaxation with Sunset Lake CBD. Head to https://sunsetlakecbd.com/coupon/sop and use code SOP for 20% off your order.  Spark something uncommon this holiday season and get 15% off the right gifts from Uncommon Goods at uncommongoods.com/sop Treat yourself and your loved ones to spa-quality skincare essentials that deliver a moisture-rich glow. Use code seeingotherpeople for 15% off at oakessentials.comTackle your toughest days by microdosing with Schedule 35 and get 15% off with code SOP at schedule35.co So, if you’re looking for a thoughtful and practical gift that he’ll actually use and love, The Chairman™ Pro is the way to go! Get 20% off + free shipping on The Chairman & with the code SOP at Manscaped.com Learn more about your ad choices. Visit megaphone.fm/adchoicesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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